JPH04230251A - Alkenylsuccinic acid monoamide salts and use thereof as corrosion-preventing agents and emulsifiers for metal hydraulic oil - Google Patents

Abstract

The invention relates to alkenylsuccinic monoamides of the formulae <IMAGE> in which R is C13-C30-alkenyl and Me<+> is an alkali metal ion, a proton or an ammonium ion of the formula <+>NHR1R2R3 and R1, R2 and R3 are identical or different and denote hydrogen, 2-hydroxyethyl or 2-hydroxypropyl. Furthermore, the invention relates to the use of these alkenylsuccinic monoamides as anticorrosives in water- and/or mineral oil-containing formulations, if desired together with ethoxylates and/or fatty acid alkanolamides, and to water- and/or mineral oil-containing anticorrosives containing alkenylsuccinic monoamides of this type.

Description

[Detailed description of the invention]

0001

FIELD OF THE INVENTION This invention relates to alkenylsuccinic acid monoamide salts and their use as corrosion inhibitors and emulsifiers for metal hydraulic fluids.

0002

BACKGROUND OF THE INVENTION 20-50% corrosion inhibitors and emulsifiers and 80-20% naphthene-based, paraffin-based
Corrosion inhibitors and emulsifiers in metal-hydraulic fluids containing base or mixed-base mineral oils should meet the following requirements:

These include clear corrosion protection against ferrous metals, emulsifying power against mineral oils, and, in combination with selected non-ionic compounds, foaming or rapid foam collapse, inhibition of microbial growth.

[0004] Only some of these requirements
This is not achieved by the compounds listed in European Patent No. 0,127,132. This bulletin has already

[0005]

[Formula 3] (wherein R is a C6-C12-alkenyl group)
Alkenyl succinic acids of the formula and their use as corrosion inhibitors have already been disclosed.

However, these compounds have insufficient emulsifying power, and therefore the emulsifier used has an insufficient shelf life. Furthermore, emulsifiers containing these compounds tend to foam, which is therefore a disadvantage in operating procedures such as crushing, in which the emulsifiers are exposed to high mechanical influences.

The disadvantages mentioned above can be overcome by the longer chain alkenyl succinic monoamides according to the invention as described below. The emulsifier opalescence achieved with these longer chain alkenyl succinic monoamides is
It shows a finer dispersion of the emulsifier compared to the short chain one, thus indicating a longer shelf life. That is, this emulsifier can be used for a longer period of time. The longer chain alkenyl succinic monoamides according to the invention also satisfy the requirements of a low tendency to foaming and foam collapse, which are not observed in the case of shorter chain compounds.

[0008]

DISCLOSURE OF THE INVENTION Accordingly, the present invention provides the formula

[0009]

[C4] or

0010

embedded image (wherein R is C13-C3 which can be branched or straight chain)
0-alkenyl group, preferably C15-C21-alkenyl group, and Me+ is an alkali metal ion,
is a proton or ammonium ion of the formula +NHR1 R2 R3 and R1 , R2 and R3
are the same or different and are a hydrogen atom, a 2-hydroxyethyl group or a 2-hydroxypropyl group)
The present invention relates to alkenyl succinic acid monoamides represented by the formula and methods of using them as corrosion inhibitors.

The preparation of alkenylsuccinic anhydrides used as starting materials from olefins and maleic anhydride is known. The alkenyl succinic monoamide is obtained by reacting 1 mol of alkenyl succinic anhydride with at least 2 mol of ammonia, and the alkenyl succinic monoamide is obtained in the form of an ammonium salt. When aqueous ammonia is used, ammonium salts of alkenylsuccinic acid monoamides are formed in the aqueous solution. Other salts of the above monoamides can be prepared by replacing ammonia with other bases. Particularly preferred salts for use as corrosion inhibitors include alkanolamines, such as triethanolamine or triisopropanolamines, which are prepared by first reacting the ammonium salt formed in an aqueous solution of the alkanolamine at elevated temperatures. Manufactured by

The liberated ammonia can be completely removed by heating the aqueous solution of the alkanolamine and then passing a vigorous stream of nitrogen through the solution. The removal of ammonia can be supported by additionally distilling off a certain amount of water, which makes it possible to obtain a certain concentration of active substance at the same time.

The alkenylsuccinic acid monoamides mentioned above are clearly water-soluble or give products that are easily emulsifiable with mineral oil. These products can be used as corrosion inhibitors in aqueous cooling lubricants, cutting and rolling fluids. These aqueous cooling lubricants are prepared by stirring or mixing the reaction products into the required amount of water and emulsifying the resulting concentrate in water. The concentrations used in drill, shear and roll fluids are about 0.1-10% by weight, preferably 2-10% by weight. The abovementioned concentrations refer to their use on their own as well as to the abovementioned combinations with mineral oils.

The emulsifier concentrate contains additional auxiliaries to optimize the emulsification behavior and corrosion protection. An example used for this purpose is the formula R4 -O-(CH2 -CH2 -O)n H, where R4 is a C10-C20-alkyl, alkenyl or alkylphenyl group and n is 2-10
) and/or an epoxylate of the formula R5 -CO-NR6 R7 (wherein R5 represents the number of
10-C20-alkenyl group, and R6 and R7 are the same or different, hydrogen atom, 2-
Examples include fatty acid alkanolamides represented by a hydroxyethyl group or a 2-hydroxypropyl group. These products can each be present in the emulsifier concentrate in amounts of about 20-40%.

[0015]

[Example] Example 1 Triethanolamine/sodium salt of pentapropenyl succinic acid monoamide 300 g of purified water and 300 g of (
A 25% strength ammonia aqueous solution (4.4 mol) is first introduced into a four-necked flask equipped with a distillation neck, dropping funnel, thermometer and stirrer, and the mixture is cooled to 0°C. 696 g (2.0 mol) of pentapropenyl succinic acid are then added over a period of 30 minutes while maintaining the temperature at 10-20° C. with cooling. After the addition has ended, the mixture is stirred for a further 3 hours at 30°C.

298 g (2.0 moles) of triethanolamine were added to the ammonium salt solution and then
96 g (1.2 mol) of NaOH (50% strength) are added. The mixture is heated slowly (approximately 2 hours) with stirring to allow the ammonia to escape and the olefin to distill off. about 1 with an active compound content of about 80%
090 g of dark liquid are obtained. The crude pentapropenyl succinic anhydride used in this example had the following main composition: Pentapropenyl succinic anhydride
Approximately 57% hexapentapropenyl succinic anhydride Approximately 10% heptapentapropenyl succinic anhydride approximately 3%
pentapropylene
Approximately 22%.

Example 2 370 g of the product obtained in Example 1, 310 g of tall oil fatty acid diethanolamide, 160 g of oleyl alcohol polyglycol ether (2 moles of ethylene oxide) and 160 g of nonylphenyl polyglycol ether (2 moles of ethylene oxide) mol of ethylene oxide) at room temperature and stir until a clear solution is formed.

Comparative Example A Triethanolamine/sodium salt of tripropenylsuccinic acid monoamide 150 g purified water and 150 g (2
．． A 25% strength ammonia aqueous solution (2 mol) is first introduced into a four-necked flask equipped with a distillation neck, dropping funnel, thermometer and stirrer, and the mixture is cooled to 5°C. 224 g (1.0 mol) of tripropenylsuccinic acid are then added dropwise over 15 minutes while maintaining the temperature at 10-20° C. with cooling. After the addition has ended, the mixture is stirred for a further 3 hours at 30°C. 149g (1.0
mol) of triethanolamine and then 48 g
(0.6 mol) of NaOH (50% concentration) is added. While passing this mixture through a nitrogen gas solution,
Heat to 110°C over time. 299 g of ammonia are distilled off at 110° C. over a period of 2 hours. The solids content is brought to 79% with 83 g of water. 469 g of product are obtained with a moisture content of approximately 18%.

Comparative Example B Triethanolamine/sodium salt of tetrapropenylsuccinic acid monoamide 150 g of purified water and 150 g of (
A 25% strength ammonia aqueous solution (2.2 mol) is first introduced into a four-necked flask equipped with a distillation neck, dropping funnel, thermometer and stirrer, and the mixture is cooled to 0-5°C. Then, 266 g (1.0 mol) of tetrapropenyl succinic acid are added dropwise over 15 minutes while maintaining the temperature at 10-20° C. with cooling. After the dripping is finished,
The mixture is stirred for a further 3 hours at 30°C. 149g
(1.0 mol) of triethanolamine are added, the mixture is stirred for 5 minutes, and then 48 g (0.6 mol) of NaOH (50% strength) are added. The mixture was heated to 110°C for about 1-2 hours while passing through a nitrogen gas solution.
Heat to ℃. 270 g of aqueous ammonia are distilled off at 110° C. over a period of 2 hours. The solids content is brought to 80.8% with 48.8 g of water. Weight: 494g.

Comparative Example C 370 g of the product obtained in Comparative Example A, 310 g of tall oil fatty acid diethanolamide, 160 g of oleyl alcohol polyglycol ether (2 moles of ethylene oxide) and 160 g of nonylphenyl polyglycol ether (2 moles of ethylene oxide) mol of ethylene oxide) at room temperature and stir until a clear solution is formed.

Comparative Example D 370 g of the product obtained in Comparative Example B, 310 g of tall oil fatty acid diethanolamide, 160 g of oleyl alcohol polyglycol ether (2 moles of ethylene oxide) and 160 g of nonylphenyl polyglycol ether (2 moles of ethylene oxide). mol of ethylene oxide) at room temperature and stir until a clear solution is formed.

[0022]

[Table 1]

[0023]

[Table 2]

Claims (5)

[Claims] Claim 1: A compound of the formula [Image Omitted] or [Image Omitted] (wherein R is a C13-C3 which can be branched or straight chain)
0-alkenyl group, preferably C15-C21-alkenyl group, and Me+ is an alkali metal ion,
is a proton or ammonium ion of the formula +NHR1 R2 R3 and R1 , R2 and R3
are the same or different and are a hydrogen atom, a 2-hydroxyethyl group or a 2-hydroxypropyl group)
Alkenyl succinic acid monoamide represented by. 2. Use of the alkenylsuccinic monoamides of claim 1 as corrosion inhibitors in water- and/or mineral oil-containing formulations. 3. Formula R4 -O-(CH2 -CH2 -O)n H, where R4 is a C10-C20-alkyl group, alkenyl group or alkylphenyl group, and n is 2-10
) and/or an epoxylate of the formula R5 -CO-NR6 R7 (wherein R5 represents the number of
10-C20-alkenyl group, and R6 and R7 are the same or different, hydrogen atom, 2-
The alkenylsuccinic acid monoamides of claim 1 are used as corrosion inhibitors in water- and/or mineral oil-containing formulations together with fatty acid alkanolamides of the hydroxyethyl group or 2-hydroxypropyl group. Method. 4. A water- and/or mineral oil-containing corrosion inhibitor containing the alkenylsuccinic acid monoamide of claim 1. 5. A water- and/or mineral oil-containing corrosion inhibitor containing from 0.1 to 10% by weight of the alkenylsuccinic acid monoamide of claim 1.